HostFleet Let’s talk

For STR operators with 10–200+ properties

The AI upsell engine for
short-term rental portfolios.

We automate upsell offers, payment collection, and cleaner coordination
across your entire portfolio to maximize your revenue per month.

Let’s talk →

Built for portfolios on

The problem with manual upsells.

Every reservation calendar is full of upsell opportunities. Catching them by hand - across every booking, every day - is impossible at scale.

01

Finding the opportunity.

Early check-ins, late checkouts, stay extensions - every reservation hides revenue. Spotting which guest to offer what, on which booking, across your whole calendar, is more than anyone can track by hand.

02

Making the offer.

An upsell only earns if it reaches the right guest at the right moment for the right price. Sending those offers manually, one reservation at a time, means most never go out - and the revenue quietly walks.

03

Coordinating the operations.

Every yes kicks off work: collect payment, update the reservation, sync the new dates to your channels, and reschedule the cleaner. Miss one step and you’ve got a double-booking or a cleaner at an occupied door.

How it works

We automate all three.

The three things that are impossible to do by hand at scale - now running automatically across your whole portfolio.

  1. 01 Scan

    Each morning, HostFleet scans your calendar for every upsell opportunity.

  2. 02 Offer

    It sends each offer to the relevant guest, at the right moment.

  3. 03 Handle

    When a guest says yes, HostFleet takes it from there:

    • → Collects the payment - Stripe link or your booking platform
    • → Updates the reservation
    • → Reschedules the cleaner and notifies them if needed

Every day, across every property - on autopilot.

Nate, Founder of HostFleet

Meet the founder

Hi, I’m Nate 👋

I built HostFleet after seeing operators struggle with proper brand presence and consistent revenue.

  • ✦ Trusted by managers of 100+ unit STR portfolios to reclaim hundreds of hours annually.
  • ✦ Experience deploying AI systems across $600M institutional real estate portfolios.

You work directly with me from day one for setup, optimization, and support. Fast, direct, and accountable.

As featured in

  • Associated Press

From first call to running system.

  1. Step 01

    Fit call

    A 15-minute call. We learn your portfolio and show you what the engine can earn. You decide if it’s a fit.

  2. Step 02

    We set up your engine

    We handle the setup. Your offers, pricing, payment collection, and cleaner coordination - all tuned to how you run.

  3. Step 03

    End-to-end test

    We run the engine end to end, with you on the line. One real upsell: offered, paid, and booked. You see exactly how it works before launch.

  4. Step 04

    Go live

    You start in manual approval mode. Every offer waits for your okay. When you’re ready, switch to auto-send and the engine runs itself.

Ready to own your booking channel?

Book a 15-minute fit call. We’ll audit your portfolio, show you what we’d implement, and demonstrate the revenue you can expect month over month.

Let’s talk →
Let’s talk →